Cap Watkins is the VP of Design at BuzzFeed in New York. He told me how he ended up in his current role and some of the growing pains along the way that influenced his career as a designer and eventually a design manager. My favourite thing about talking with Cap is how reflective he is on what he's learned so far, which is probably credit to all of the writing he does on his own blog. He talks about the transition into his role at BuzzFeed, why he loves managing a team and advice for designers on when it's time to move on from something. Cap's experience mixed with his lighthearted humor made for a great conversation, with loads of insight.

Tell me a little bit about your current role and the work that you're doing right now?

I'm the VP of Design at BuzzFeed in New York. That's my title. What do titles even mean? [laughs] What I'm responsible for is the product design team which is 16 designers at the moment. The product design team covers the site, our apps as well as our internal tooling that we use for data analysis and ad sales. I also manage the consumer branding team, which works on logos, the style guide, and swag. If you ever see someone with a BuzzFeed T-shirt or something, we probably designed it.

I know that you were at Etsy and other companies previously. What was the path to your role now?

It was very long and fraught with danger.

I graduated college with a creative writing major and had taught myself HTML during that time. When I finished school I got a job at a coffee shop like all good creative writing majors because I didn’t know what I wanted to do with my life [laughs]. I was doing some web work on the side and did a website for a couple of my friends from college who were starting a company. One day they called me and said, “hey, we got funded!” They needed a designer and asked if I wanted to move to Oakland. I said yes and three days later I packed up my things and moved. That company was PMOG and was a Firefox extension that essentially turned your internet browsing into an MMO game. It was really cool.

After that I took a job at Zoosk, an online dating company. I was the only designer there for about two years. In my first job I’d learned a lot about having to write production CSS and deploy things but at Zoosk I wound up learning a lot more about the design process itself. The founders had been working at Microsoft before that, so they'd actually seen design in a professional context. They knew a lot about user testing, things like AB-testing, user flows and that was all new to me.

When I left that job I went to Formspring which was hot on the internet for about 20 minutes. I was also the only designer there for a couple of years until it was pretty clear that we weren’t going to make it. It was fun because I’d never worked on a social product before. The thing that made Formspring so viral in the beginning was that you could ask someone a question anonymously. Anonymity, turns out is a super viral thing. The problem was that it made it too easy for people to abuse each other and we saw a lot of that, a non-trivial amount. We considered turning the ability to do that off, or changing the settings so you could only allow anonymous questions if you wanted to, but we wound up not doing either. That’s the hard part, that’s where the majority of the traffic was coming from, so we spent a lot of time not addressing what was the real problem with the product. It was in that role that I really thought about what was important to me as a designer for the first time.

I started thinking a lot about the product and not just the job, and what I wanted to do next. I thought about what products I really liked myself and what I thought was good for the world and impactful. This was around the time that the second Kindle came out, which I still think is the peak Kindle. I found myself reading a lot more because I had access to all of these books. Amazon Prime was skyrocketing at that point too and it just seemed like they were doing interesting work. I found one of the design directors at Amazon on Twitter and followed him hoping he’d follow me back. He did and I DM’d him. We had a phone call that went really well so they flew me into Seattle for an interview. They wouldn’t tell me what they were working on, it was a secret project. Sidenote: If you’re ever trying to hire a designer just tell them it’s a secret project - I couldn’t take not knowing. I took that job and moved to Seattle to work for Amazon. It was the first time I’d really worked with other designers before, after having been the only designer in so many of my past roles. So you walk in thinking you know what you’re doing and you definitely don’t. It was clear so quickly that these people were way smarter than me. It was kind of awesome.

There was one guy in particular, Aaron Donsbach, he was a principal designer at Amazon and he was just one of those people that you know you want to know. Super smart guy. We didn’t sit near each other so every morning I’d go sit by his desk and just talk to him. He was either going to tell me to go away and stop being annoying or he was going to be my friend [laughs]. We’d be working on these hard systems problem and get really deep into it and realize that one piece of it undid everything else in the system. I learned a lot from him about being able to step away and view my work dispassionately, which is a really hard thing to do.

Three years ago I ended up moving to Brooklyn and taking on a design manager position at Etsy. I found being in a leadership role there was a lot of freedom to be the kind of manager I wanted to be. I’ve found that I enjoy the management part a lot more than I think I ever even enjoyed design. You hire these talented people and the worst thing that could possibly happen is that they can’t do their best work. I like the idea of smoothing the path for designers so they can just do their absolute best work.

So I spent a couple years at Etsy and then I met a couple BuzzFeed designers and started talking to them. Now I’m the VP of Design at BuzzFeed. It still feels surreal when I say it.

You've moved around a lot and had a lot of different experiences, how do you know when it's time for a new challenge for yourself. When it's time to move on and do something else?

I think there are a couple of factors. One, is that every place you ever work is going to have problems and challenges to solve, no matter what. I've come to terms with the fact that there are no perfect companies. People look for that a lot, I was looking for that a lot, and it doesn't exist.

No place is free of challenges. Buzzfeed has challenges, problems we're trying to solve, things we're not happy about internally, it's true everywhere. I think one of the big things for me is: are the problems and challenges that I'm facing in my job, problems and challenges that I find valuable to solve? That’s an important question to ask.

The second thing is: how empowered am I to solve them? I think there's a point where you're maybe solving problems that you shouldn't have to solve. That can feel really bad and might be a reason to leave. More importantly, not being empowered to solve those things, or not seeing a path forward. That is the reason to leave.

If I'm okay with the problems and challenges, no problem. If I can't actually impact them in any way, shape or form, but I'm still experiencing them all the time, that's not sustainable. Those are really the two main reasons.

In your role right now, what would you say are the most challenging aspects of what you're doing?

One thing that has been challenging for sure is managing all these different disciplines and areas that I haven’t tackled before. When I came to BuzzFeed we didn’t have a branding team. So I created one and found this designer on the team who was a really great illustrator, I grabbed him and the two of us formed the branding design team [laughs].

I wasn’t about to send an email to all BuzzFeed employees saying, “There is a branding team now and you need to go through us!” That’s completely bonkers. So instead we took a more “grass-rootsy” approach. I was in a lot of conversations so if I heard something we could help with I’d say, “cool, we could do that for you” or “we could help you with that.” We’d do great work for them (and by we I mean Shaun, the illustrator), we’d communicate well and the work would go out. Then someone else would see it and ask where it came from, and I’d get an email: “Hey I heard there’s this thing that exists, could we get something from you for this thing we’re doing?” That expanded much faster than I expected it to so we hired another guy, Chris Rushing, who is now the senior art director and helping me run all of that. That could have all blown up in my face. We could have tried it, it could have totally fell down and then I would have walked away and pretended like it never happened. That's not what happened, and that's pretty awesome.

The other hard thing is, we've grown so fast. The company doubled the size last year in 2015. Communication, it's hard anyway, and it becomes more complicated, the larger you get. I'm still figuring out the best way to communicate across all of these different teams and trying to keep up with them and make sure that we're talking regularly. It has already become more of a challenge. That'll be a time and iteration thing where it's just like we'll try some stuff and see what works and what doesn't work; figure out the best balance.

As VP, you're wearing a lot of different hats, managing a lot of different roles and disciplines and trying a lot of different things. From a perspective of either a typical day or typical week, how are you dividing up your time to focus on all the different things that you need to do?

The priorities for me are shifting so quickly. I’m always making sure I’m being proactive but what the things are that I'm being proactive about are shifting week by week.

Some weeks I’m focused on the CSS framework that we’re building and trying to get that out the door or trying to organize training sessions for all the people that will need to use that framework. Another week it might be coordinating holiday swag for all the employees at BuzzFeed. Another week I’ll prioritize communicating with the teams and making sure everybody feels good about where we’re headed. In a few weeks we’re moving offices so that’s been a project we’ve been working on.

Every week is different but there are some things that occur every week, such as one-on-one’s with folks I directly manage or just people who want to check in with me regularly. We have a critique every week as well. Those things kind of happen with frequency and cadence. Other than that it changes every single week for me which I really enjoy.

Is there anything you do to keep a routine or section off time to do certain things that have to happen regularly?

There are a couple things that I schedule for myself pretty regularly. Once a month I book an hour out for myself. It just recurs every month. I call it monthly reflections. I have a doc and I just pop it open and I have the name of each person I’m managing in it and I write a quick 3 or 4 sentences about what's happened in the last month. What I've been thinking about with that person. It's a log for me. It makes things like quarterly reviews or mid-year reviews much simpler.

I try to leave my calendar as open as possible because in my opinion, my job as a manager is to be available. I tell all the designers, even the ones that I don't manage directly, I'm like, "Hey look, if you need time, if you want to talk to me for any reason whatsoever. My calendar is your calendar. Put time on there, just take it".

Was there a time most recently where you did something that made you uncomfortable or scared you or took you out of your comfort zone? What was that and how did you deal with that?

Taking this job scared me for sure. Have you heard of the Peter Principle? It's this idea that everyone gets promoted until they get to the position that they're no longer useful and that's where they stay. They stay in a position where they're no longer useful. I'm always worried whenever I move to the next level of something that I'm about to hit that point. I get asked sometimes, "Wouldn't it be cool to be Chief Design Officer or something"? I'm like, "Well I don't know". That sounds terrifying. What if that's the job? What if that's the job where I become completely useless? It’s totally possible. I don't want that to be true. Taking this job scared me a lot in that way but I also think that you should do those things, probably.

Mostly though, I’ve come to the realization that nothing is really scary as long as it’s changeable. If I can change it once I realize it’s not working, it makes things way less scary.

What would you say are the five tools that you're using on a regular basis, kind of every day that help you do what you're doing?

Slack - I don't know what we would do if we didn't have it. The world would be a terrible place. I'm really glad that somebody productized IRC and made it way more friendly than it actually is.

Omnifocus - There are a lot of people who are very hardcore about to-do management. I am not that person. I keep it for very simple lists of things which may be a stupid reason to pay for Omnifocus but I really like it.

Gmail - I think the people that are bummed out about it don't use it correctly. It's a to-do list for me. If it's in my inbox, I need to deal with it. I am an inbox zero person. I try to get to zero.

Google Apps - We're deep in Google Docs here. I love it. I love the simplicity of sharing things with people, and the ability to collaborate on docs together.

Sublime Text - For the CSS framework we’ve built, I'm pretty involved in that. For me it's like a fun side project to work on and chew into every now and then.

How do you manage your time amongst communications and email versus other work you need to do?

If I have a few minutes between meetings I'll check in on email, not to respond to it, but to curate it out; and just keep it clean so when I do sit down to look at it I’ll have a pretty actionable list of things to do.

The only thing that I can think to say is that Slack is really helpful in that way. I do tend to pop by people's desks randomly too. If I'm walking by, I'll pop in and see how it's going. Being on Slack actually makes me still available if I'm sitting at my desk and chewing through emails. If someone goes, "Hey, do you have a minute?” I'll just put it down and stand up and walk over. I don't need to keep doing email.

I feel like it's a self-management problem a little bit. The people that I know that are drowning in email, could probably not drown. It seems achievable to put yourself in a position to not have that happen. It's a lot of discipline and committing to it. I think, if you think of email like chat or something, you're screwed. You're just going to let it all pileup.

Why do you love what you do and what makes the work that you do meaningful to you?

There's so many reasons. At this point in my career, I really value good communication and healthy teams, which go hand-in-hand. I love the job I have right now because I'm in a position to really make an impact in that way. It’s also really empowering and really exciting because if a designer is having a hard time, I can do something about that. I love that about this job.

I love that if for some reason, tomorrow the way we're doing design critique was completely broken all of the sudden, we just all realized at the same time like holy crap this isn't working. There's no system for me to go through to change it, I can literally talk to the designers and figure out something to try and try it. That's super cool, I love that. I love working with the designers, I love who we hired, I love who’s here.

We have such a really solid team. Everyone on the design team is so generous with their time and their work. No one is precious about it. It's really exciting time to be at Buzzfeed too. We're growing so quickly. We're doing all sorts of new things all the time. It's just very exciting. Like I said, every week's completely different, there's never a dull week. It's never not exciting. It's never not interesting. I really love that.

Who would you want to see on Ways We Work?

Andrew Crow - Head of Design at Uber, I’d love to know how it’s going and how their team is working.

Brynn Evans - She was a designer on Google+, she’s also now working on Google Fi. I heard her speak once about why she works on the problems she works on. I’d love to hear more from her about how she likes to work.

Aaron Donsbach - He was my mentor at Amazon, he's still a really close friend of mine. He's a really excellent design mind. He's working at Google now in Seattle. He's just one of those people that I feel like more people should know.